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In the course of CHRIS ISAAK’s career, he has released nine extraordinary albums, twelve singles, been nominated for two Grammy awards, acted in several motion pictures, and starred in his own critically acclaimed TV series. His legendary shows with his longtime band Silvertone have entertained tens of thousands of people for over two decades. Even his hair has its own fan club. And yet, this highly praised platinum-selling artist had never released a greatest hits album… until 2006.

Hard to believe? Well, unlike some artists who roll out a greatest hits package after, say, their second album, Isaak waited until he actually had enough hits to legitimately describe the collection as such. “Shouldn’t a greatest hits collection after two records be called ‘Greatest Hit’?” Isaak asks. “I guess I’ve just always been too busy making records. Plus, it takes a while before you really want to compile everything. But after going through all the songs to make the Best Of, I feel like we have good stuff.”

Good stuff. That’s typical Isaak self-deprecation – it’s much more than good stuff. Best Of Chris Isaak (2006) – the CD and accompanying DVD, which features 18 video clips by such esteemed directors as Gus Van Sant, Bruce Weber, Herb Ritts, Mary Lambert, and Jean-Baptiste Mondino – take listeners on a gratifying musical journey through the Stockton, California native’s two-decade career, showcasing his stellar songwriting; smooth, dusky baritone (and tender falsetto that will alert your dog); and effortless brand of stylish retro-cool.

The album displays Isaak’s many different musical personas: the rockabilly rebel (“Dancin’,” “Baby Did A Bad, Bad Thing,” “Speak Of The Devil”), the brokenhearted crooner (“Wicked Game,” “Somebody’s Crying”), and the breezy acoustic storyteller (“San Francisco Days,” “Two Hearts”). It includes two brand new songs, the elegant “King Without A Castle” and the break-up exhortation “Let’s Have A Party,” as well as two covers: Cheap Trick’s power-pop anthem “I Want You To Want Me,” a live favorite previously unavailable on any of his CDs (“It’s kind of fun to do something a little different for me,” Isaak says), an inspired version of his hero Roy Orbison’s classic lovelorn ballad “Only The Lonely,” and a stirring never-before-heard acoustic version of “Forever Blue.”

“What a sweet guy Roy was,” Isaak says. “We opened for him one time and after the show I said to him, ‘I don’t know if I write hits or not,’ and he said, ‘You write hits, you just don’t know it.’ It was exactly what I needed to hear at the time to keep me going for another year.”

That was before noted director David Lynch used “Wicked Game,” a spare, moody ballad from Isaak’s third album, Heart-Shaped World, in the film Wild At Heart. The song went Top-10 in 1991, and the video, a steamy Herb Ritts-directed clip featuring the singer rolling around on the beach with a topless Helena Christensen, made Isaak a star. “‘Wicked Game’ really put us out there,” he says. “We were on the road at the time, and got to ditch our van and get into a bus. For the first time in years, we got some sleep!”

Then there’s the swaggering, bluesy rocker “Baby Did A Bad, Bad Thing” (also from Forever Blue), which can be heard in Stanley Kubrick’s 1999 film Eyes Wide Shut starring Tom Cruise and Nicole Kidman. The director asked Kidman what music she wanted to rehearse the movie’s striptease scene to. “Nicole had been listening to the track and brought it in to run through for her rehearsal,” Isaak recalls. “Stanley said, ‘I love it,’ and put it in the film. I owe Nicole Kidman a full-body massage.”

While reviewing tracks, some going back to the mid-’80s, Isaak says what struck him most was how lucky he has been to have the people he works with around him, such as producer Erik Jacobsen (“who taught me everything I know about making records, but not everything he knows”), longtime engineer Mark Needham, and his Silvertone bandmates, drummer Kenney Dale Johnson, bassist Rowland Salley, and guitarist Hershel Yatovitz, who have been with Isaak for years. “People see my picture on the album covers and think, ‘Chris goes into a room and he makes an album.’ But I go into a room and make it with these guys, who’ve been supportive, and have good ideas and good energy.”

And to what does he attribute the longevity of his career? “You know, I’ve never tried to jump on a trend, and I’ve never had to jump off of one,” he says. “I try to do what feels right for each song. So I never have to go, ‘Well, no more disco for me’.”

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